Here's the video version of this newsletter:

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“Sell me this pen”.

You’ve probably heard of this infamous sales interview question (it was also referenced by Leonardo DiCaprio a few times in the movie ‘The Wolf of Wallstreet’).

The challenge here is to take something dull and make people feel something about it.

At first glance, it’s just a pen. But a great salesperson doesn’t sell the object—they sell the possibilities. They make you imagine:

• the love letter you’re writing
• the contract you’re signing
• the legacy you’re creating

Now, what if I told you Dropbox did exactly that—but with file storage?

Asking the right questions

They hired a creative agency - Instrument, which conducted some interviews to ask Dropbox users about their experience with file storage.

But as they went down this rabbit-hole and collected more stories, they had a sudden realization:

From that point, instead of asking about their experience using the product, they asked: “What are your most important files and folders?”.

It was from these stories that they launched a campaign that would make you feel emotional about file storage.

What they did

In 2021 Dropbox launched the “For All Things Worth Saving” campaign.

The genius of this campaign? It wasn’t about files or the cloud—it was about the human stories behind those files:

Why this worked

1. Aspiration > features

Instead of explaining “how Dropbox works,” they showed why it matters by sharing real customer stories.

They didn’t say, “Store your files here.” They made you think about what those files represented:

• Family memories you’d pass down for generations
• Creative work that could change the world
• Moments that can impact society

When you save what matters, you’re not just using Dropbox. You’re part of a bigger story about protecting the things that make life meaningful.

This is one step above outcomes or benefits.

2. Social proof

That designer? That activist? That artist?

If those heroes trust Dropbox, you should too.

Showing real people using your product is one thing, showing who uses it amplifies trust even further.

The Takeaway

It’s like the "sell me this pen" concept. People don’t care about the product itself—they care about the possibilities it unlocks.

Dropbox figured this out: People don’t care about what you do until they care about why you do it.

So, whether you’re running a startup, building a product, or pitching your next big idea, here’s the golden rule:

Make it aspirational. Show them the why.

P.S But sometimes, this isn’t enough. You’ll need to include your competitors in your storytelling to convince them why your product is better. Watch this video to learn how Apple did just that.​

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